Water → HCID 12795550, compound

HRID 980186Notes

Reaction equation

HRID 980186 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:9]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:27])[CH2:25]Br)=[CH:20][CH:19]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>C(N(CC)CC)C.CN(C)C=O>[C:9]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:24](=[O:27])[CH2:25][N:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[N:6][C:5]2=[O:8])=[CH:22][CH:23]=1)(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 12537708N-[4-(Bromoacetyl)phenyl]benzamide

Product 1

HCID 12795550HCID 12795550, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 5-chloropyrimidin-2-one (338 mg) and 4'-benzamido-2-bromoacetophenone (766 mg) in triethylamine (1 ml) and dimethylformamide (10 ml) was stirred at ambient temperature, giving a solution, quickly followed by formation of a precipitate. After 45 mins, water (100 ml) was added to the suspension. The collected solid was crystallised from glacial acetic acid to give the title pyrimidinone (439 mg,); m.p. 290°-303°; λmaxEtOH 226 nm (ε 16230), 302.5 nm (ε 20370).

Workup

  1. customgiving a solution
  2. customThe collected solid was crystallised from glacial acetic acid

Sources & evidence

ORD record
ord-19343eca45de4de2b7471de3fe432f1b
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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